CN105044177B - Click chemistry technology prepares molecular engram paper chip sensor - Google Patents
Click chemistry technology prepares molecular engram paper chip sensor Download PDFInfo
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- CN105044177B CN105044177B CN201510480233.0A CN201510480233A CN105044177B CN 105044177 B CN105044177 B CN 105044177B CN 201510480233 A CN201510480233 A CN 201510480233A CN 105044177 B CN105044177 B CN 105044177B
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Abstract
Paper chip print pattern is designed using Adobe Illustrator CS4, using on wax spray printer bulk print pattern to paper, it heats wax and melts the hydrophobic wall of making, by screen printing technique printing work electrode, reference electrode and to electrode, gold nano grain is grown using seed mediated growth method paper fiber surface.Alkyl azide mercaptan is fixed on paper fiber gold nano-material surface, it is reacted by carrying out click chemistry with acrylic acid propynyl ester, the function monomer of selection synthesis organophosphorus insecticide molecularly imprinted polymer, by the amount of certain substance than by the template molecule of organophosphorus insecticide, function monomer, quantum dot, crosslinking agent, pore-foaming agent, initiator and organic solvent are uniformly mixed, induced polymerization reacts under 365nm ultraviolet lights, prepare paper fiber molecular imprinted polymer on surface film, high selection to organophosphorus pesticide is realized using photic electrochemical method, it is highly sensitive, low cost and immediately detection.
Description
Technical field
The present invention relates to the Detection Technologies of Pesticide Residues field, more specifically a kind of light that can detect organophosphorus pesticide
The preparation of chemical paper chip sensor is sent a telegraph, the invention further relates to using trace pesticide in the molecular imprinting technology determination sample
Remaining method.
Background technology
Pesticide is widely used in control or eliminates agriculture, forestry pests ＆ diseases a kind of organic compounds, due to Pesticide use
Range is more and more wider, and frequency of use is higher and higher, and amount of application is increasing, it has also become contaminated food products pesticide the most serious.Agriculture
Medicine residual is exceeded not only to pollute agricultural product and ecological environment, will also jeopardize health and life security.Organophosphorus pesticide is mesh
A kind of pesticide widely applied, organophosphorus pesticide enter organism, have inhibition to cholinesterase in organism in preceding pesticide
Effect inhibits cholinesterase that it is made to lose the ability for decomposing acetylcholine, causes acetylcholine to accumulate, cause nervous function disorderly
Disorderly, so as to cause the damage to human body.
The method for establishing a kind of highly sensitive and specificity Rapid Screening organophosphorus pesticide object, becomes currently should
One of the problem of research field urgent need to resolve.Current existing organophosphorus pesticide analyte detection or screening methods include mainly master
To include chromatography, enzyme inhibition, immunological method etc., but these are detected or screening methods Shortcomings.
Thin-layered chromatography is easy to operate, qualitative accurate convenient for grasping, but quantitative determination accuracy and sensitivity are low, are
A kind of common qualitative determination method.Although chromatography mass spectrometry detection sensitivity is very high but price is relatively expensive, and chromatography is examined
Rising limit is higher, cannot meet the actual needs of trace pesticide residue and export trade detection, therefore usually requires before analysis
It is enriched with, the difficult point of complicated food and agricultural product isolated and purified is sample substrate complexity, and interfering substance is more, pre-treatment step
It is rapid comparatively laborious.
Enzyme inhibition is easy to operate, and speed is fast, is not required to expensive instrument, is particularly suitable for the sieve of Site Detection and gross sample
Selected Inspection is surveyed, but sensitivity is poor, and different to the sensitivity of all kinds of different detection of organic phosphorus pesticide, and repeatability, the rate of recovery are also
It is to be improved.
Enzyme-linked immune analytic method detects the high sensitivity of organophosphorus pesticide, and accuracy is high, the high specificity of method,
It is convenient and efficient, but to the high selectivity of reagent, corresponding artificial antigen is synthesized when being detected for small-molecule substance, half
Not only heavy workload, period are long for antigen synthesis, but also different journeys may occur for the similar pesticide of structure or pesticide metabolism object to be measured
The cross reaction of degree.
For several detection methods of organophosphorus pesticide in food, compared to respectively there is quality, wherein in organophosphor agriculture
Medicine inspection requires that detection sensitivity is high, sample handling processes are simple, processing speed is fast, use device wants small, to measuring in advance in surveying
The selectivity and the rate of recovery of component want high.In the case, new detection technique or sample pretreating method are by positive exploitation
Out, the photic electrochemical sensor of molecular engram paper chip prepares and its is used for detection of organic phosphorus pesticide.
Invention content
The object of the present invention is to provide click chemistry technologies to prepare molecular engram paper chip sensor, and the present invention uses refill
Piece is carrier, using click chemistry technology for preparing molecular blotting ploymer film, establishes the photic electrochemistry paper of organophosphorus pesticide
Chip sensor rapid detection method has been successfully established the sensing of sensitive, quick, special, live instant detection organophosphorus pesticide
Device.
In order to solve the above-mentioned technical problem, the present invention is realized by following measures：Click chemistry technology prepares molecule
Trace paper chip sensor, it is characterized in that including the following steps：
（1）Adobe Illustrator CS4 are used to design paper chip hydrophobic wax bulk print pattern, pattern on computers
As shown in Fig. 1, paper is cut into A4 sizes, the paper cut out is placed into wax spray printer, hydrophobic wax bulk print pattern
It prints on paper；
（2）By step（1）In be placed into constant temperature oven with the paper of wax pattern, heat 0.5- under 60-150 degrees Celsius
2 minutes；
（3）In paper base material hydrophilic region by screen printing technique printing work electrode, reference electrode and to electrode；
（4）By step（3）Batch paper chip is cut into single paper chip after processing, and gold seeds solution, which drops to, is printed on working electrode
Back side hydrophilic region, be incubated 0.5 ~ 1 h, be added 20 μ L contain gold chloride, hexadecyltrimethylammonium chloride and hydrogen peroxide
Phosphate buffer solution, be incubated 5 ~ 10 minutes, paper fiber surface grow gold nano grain；
（5）Alkyl azide mercaptan, the 10 μ L 2mmol/L nitrine undecyl sulphur of μ L ~ 15 are fixed in paper fiber gold nano surface
Alcohol is added dropwise is incubated 8 ~ 12h in paper chip working region, then uses redistilled water washes clean, nitrogen drying；
（6）By being reacted with acrylic acid propynyl ester click chemistry, to step（5）Processed working electrode area is added 5
The μ L 2mmol/L acrylic acid propine ester solutions of μ L ~ 10, and 0.5mol/L ascorbic acid and the mixing of 0.1mol/L copper sulphate is added
Liquid 10 μ L, avoid light place 10h are first washed, then second distillation water washing with methanol, are dried；
（7）The function monomer of selection synthesis organophosphorus insecticide molecular imprinted polymer membrane；
（8）Semiconductor-quantum-point material is prepared using existing method；
（9）By the amount of certain substance than by the template molecule of organophosphorus insecticide, function monomer, quantum dot, crosslinking agent, cause
Hole agent, initiator and organic solvent are uniformly mixed, and induced polymerization reacts 1h under 365nm ultraviolet lights, prepare paper fiber surface molecular
Imprinted polymer film；
（10）By template molecule in eluent molecular imprinted polymer membrane, ethyl alcohol, distillation moisture are then used successively
Not Xi Di 3 times, it is spare；
（11）By sample drop in paper chip, places 5 ~ 10 minutes, adopt and be washed with distilled water 3 times, be detected, such as Fig. 2 institutes
Show.
Paper of the present invention is the Whatman chromatographies of GE Healthcare Worldwide companies of Chinese Shanghai Pudong
Paper；
Wax spray printer of the present invention is Fuji-Xerox's wax spray printer；
Working electrode of the present invention is printed with Ag/AgCl using carbon printing, reference electrode and is printed with carbon to electrode；
Gold seeds solution of the present invention uses sodium borohydride reduction, sodium citrate to be made for protective agent；
A concentration of 10 mmol/L of phosphate buffer solution of the present invention contains 1.2 mmol/L gold chlorides, 2.0 mmol/L
Hexadecyltrimethylammonium chloride and 7.2 mmol/L hydrogen peroxide；
Of the present invention be semiconductor-quantum-point is CdTe quantum, CdSe quantum dot and CdS quantum dot；
Function monomer of the present invention is Methacrylamide, acrylamide, acrylic acid, methacrylic acid；
Crosslinking agent of the present invention is ethylene glycol dimethacrylate；
Initiator of the present invention is azodiisobutyronitrile, potassium peroxydisulfate；
Pore-foaming agent of the present invention is using acetonitrile, methanol, isopropanol；
Organic solvent of the present invention is dichloromethane or carbon tetrachloride；
The template molecule of synthetic pesticide remaining molecules imprinted polymer film of the present invention, function monomer, crosslinking agent, pore
The amount ratio of the substance of agent, initiator and organic solvent is 0.1~0.5: 5: 0.5~5: 20~55: 0.1~0.5: 1.5~30, is mixed
Enter 2mg quantum dots；
Eluant, eluent of the present invention is volume ratio 8:2 ethanol/acetone.
Click chemistry technology of the present invention prepares molecular engram paper chip sensor, beneficial effects of the present invention：
1. the photic electrochemistry paper chip sensor preparation method of molecular engram, gold nano is grown in chemically grown method paper fiber
Particle increases the specific surface area of sensing interface and the electric conductivity of paper fiber so that prepared pesticide residue molecule print
The photic electrochemistry paper chip sensor of mark has higher sensitivity and detection range.
2. using click chemistry technology molecular engram film will be prepared being modified with gold nano paper fiber surface, light is improved
Send a telegraph the selectivity and accuracy of chemical paper chip sensor.
3. photic electrochemistry paper chip sensor obtained by the present invention carries out effective minute of photocurrent carrier using quantum point
From the highly sensitive detection of pesticide residue in sample may be implemented.
4. the photic electrochemical analysis method of use of the photic electrochemistry paper chip sensor of molecular engram of the present invention, energy
The high sensitivity of enough improvement methods, simplifies instrument and equipment, improves detection speed, can realize the high pass of great amount of samples in a short time
Amount screening.
5. the photic electrochemistry paper chip sensor of molecular engram of the present invention completes detection pesticide residue in paper chip
Object greatly reduces operating cost, is convenient for Site Detection.
Description of the drawings
Fig. 1 paper chips pattern and the pattern that prints electrode, A：Auxiliary area, B：Working region, C：To electrode, D：Work electricity
Pole, E：Reference electrode.
Fig. 2 molecular engram paper chip sensor detects schematic diagrams.
Specific implementation mode
Embodiment 1：The detection of parathion-methyl
（1）Adobe Illustrator CS4 are used to design paper chip hydrophobic wax print pattern on computers, by what is cut out
Paper is placed into wax spray printer, and hydrophobic wax print pattern prints on paper；
（2）By step（1）In be placed into constant temperature oven with the paper of wax pattern, heated 1.5 minutes under 90 degrees Celsius；
（3）It is printed electrode by screen printing technique in paper base material hydrophilic region, working electrode is using carbon slurry, reference electricity
It is starched with Ag/AgCl and electrode is starched using carbon in pole；
（4）By step（3）Batch paper chip is cut into single paper chip after processing, and 10 μ L gold seeds solution, which drop to, is printed on work
The back side hydrophilic region of electrode is incubated 1h, and 20 μ L are added and contain 1.2mmol/L gold chlorides, 2.0 mmol/L cetyl front threes
10 mmol/L phosphate buffer solutions of ammonium chloride and 7.2 mmol/L hydrogen peroxide are incubated 8 minutes, the growth of paper fiber surface
Gold nano grain；
（5）Alkyl azide mercaptan is fixed on paper fiber gold nano surface, and 10 μ L 2mmol/L nitrine undecyl mercaptan are in paper
Chip electrode is incubated 10 h, then uses redistilled water washes clean, nitrogen drying；
（6）By being reacted with acrylic acid propynyl ester click chemistry, to step（5）Processed working electrode area is added 5
2 mmol/L acrylic acid propine ester solutions of μ L, and 0.5 mol/L ascorbic acid and 0.1 mol/L copper sulphate mixed liquors is added
10 μ L, avoid light place 10h are first washed 3 times with methanol, and then second distillation water washing 3 times, dry；
（7）It is prepared by CdTe quantum solution：In N2It is Te presomas by the NaHTe of existing system, with CdCl under protection2Reaction,
Under conditions of thioacetic acid is as stabilizer, the water-soluble CdTe quantum dots solution of system；
（8）By parathion-methyl, acrylamide, ethylene glycol dimethacrylate, acetonitrile, azodiisobutyronitrile and tetrachloro
Change carbon according to 0.2: 5: 2.0: 40: 0.2: 3.0, mixes 2mg steps（7）CdTe quantum is made, is uniformly mixed, 365nm is ultraviolet
Induced polymerization reacts 1h under light, and paper fiber surface is made and contains quantum dot molecular imprinted polymer membrane；
（9）By parathion-methyl in ethanol/acetone eluent molecularly imprinted polymer, then successively use ethyl alcohol,
Distilled water wash respectively 3 times, it is spare；
（10）By 10 μ L sample solution drop in paper chip, places 10 minutes, adopt and be washed with distilled water 3 times, be detected, first
The detection of base parathion linearly ranging from 2.0 × 10-12~4.3 × 10-10Mol/L, detection are limited to 1.0 × 10-12mol/L。
Embodiment 2：The detection of metrifonate
（1）Adobe Illustrator CS4 are used to design paper chip hydrophobic wax print pattern on computers, by what is cut out
Paper is placed into wax spray printer, and hydrophobic wax print pattern prints on paper；
（2）By step（1）In be placed into constant temperature oven with the paper of wax pattern, heat 2 minutes at 80 degrees celsius；
（3）It is printed electrode by screen printing technique in paper base material hydrophilic region, working electrode is using carbon slurry, reference electricity
It is starched with Ag/AgCl and electrode is starched using carbon in pole；
（4）By step（3）Batch paper chip is cut into single paper chip after processing, and 10 μ L gold seeds solution, which drop to, is printed on work
The back side hydrophilic region of electrode is incubated 0.5h, and 20 μ L are added and contain 1.2mmol/L gold chlorides, 2.0 mmol/L cetyls three
10 mmol/L phosphate buffer solutions of ammonio methacrylate and 7.2 mmol/L hydrogen peroxide are incubated 10 minutes, the life of paper fiber surface
Long gold nano grain；
（5）Alkyl azide mercaptan is fixed on paper fiber gold nano surface, and 15 μ L 2mmol/L nitrine undecyl mercaptan are in paper
Chip electrode is incubated 8 h, then uses redistilled water washes clean, nitrogen drying；
（6）By being reacted with acrylic acid propynyl ester click chemistry, to step（5）Processed working electrode area is added 10
2 mmol/L acrylic acid propine ester solutions of μ L, and 0.5 mol/L ascorbic acid and 0.1 mol/L copper sulphate mixed liquors is added
10 μ L, avoid light place 10h are first washed 3 times with methanol, and then second distillation water washing 3 times, dry；
（7）CdO is dissolved into octadecylene, it, then will be dissolved with the octadecylene of Se powder with oleic acid Hybrid Heating to 300 DEG C
It injects in above-mentioned solution, stops reacting in 3h, reactant is injected in chloroformic solution, CdSe quantum dots are obtained；
（8）By metrifonate, methacrylic acid, ethylene glycol dimethacrylate, isopropanol, potassium peroxydisulfate and carbon tetrachloride
According to 0.5: 5: 5: 50: 0.4: 20,2mg steps are mixed（7）CdSe quantum dot is made, is uniformly mixed, is lured under 365nm ultraviolet lights
Polymerisation 1h is led, paper fiber surface is made and contains quantum dot molecular imprinted polymer membrane；
（9）By metrifonate in ethanol/acetone eluent molecularly imprinted polymer, ethyl alcohol, distillation are then used successively
Water wash respectively 3 times, it is spare；
（10）By 10 μ L sample solution drop in paper chip, places 10 minutes, adopts and be washed with distilled water 3 times, be detected,
The detection of metrifonate linearly ranging from 2.0 × 10-12~4.3 × 10-10Mol/L, detection are limited to 1.0 × 10-12 mol/L。
Claims (2)
1. a kind of preparation method of molecular engram paper chip sensor, it is characterized in that including the following steps：
(1) it uses Adobe Illustrator CS4 to design paper chip hydrophobic wax bulk print pattern on computers, paper is cut out
At A4 sizes, the paper cut out is placed into wax spray printer, hydrophobic wax bulk print pattern prints on paper；
(2) paper for carrying wax pattern in step (1) is placed into constant temperature oven, 0.5-2 points is heated under 60-150 degrees Celsius
Clock；
(3) carbon working electrode, Ag/AgCl reference electrodes and carbon pair are printed by screen printing technique in paper base material hydrophilic region
Electrode；
(4) batch paper chip after step (3) processing is cut into single paper chip, gold seeds solution drops to the back of the body for being printed on working electrode
Face hydrophilic region is incubated 0.5~1h, and the phosphorus that 20 μ L contain gold chloride, hexadecyltrimethylammonium chloride and hydrogen peroxide is added
Acid buffering solution is incubated 5~10 minutes, and paper fiber surface grows gold nano grain；
(5) alkyl azide mercaptan, the 10 μ L 2mmol/L nitrine undecyl mercaptan of μ L~15 drop are fixed in paper fiber gold nano surface
It is added in paper chip working region and is incubated 8~12h, then use redistilled water washes clean, nitrogen drying；
(6) by being reacted with acrylic acid propynyl ester click chemistry, 5 μ of μ L~10 L are added to the processed working region of step (5)
2mmol/L acrylic acid propine ester solutions, and 10 μ L of 0.5mol/L ascorbic acid and 0.1mol/L copper sulphate mixed liquor are added, it keeps away
Light places 10h, is first washed, then second distillation water washing, is dried with methanol；
(7) by the semiconductor-quantum-point of preparation and organophosphorus pesticide template molecule, function monomer, crosslinking agent, pore-foaming agent, initiator
It is uniformly mixed with organic solvent, induced polymerization reacts 1h under 365nm ultraviolet lights, passes through eluent molecular imprinted polymer membrane
Then middle template molecule is washed 3 times with ethyl alcohol, distilled water, prepares molecular imprinting of organophosphorus pesticide residue polymer respectively successively
Film, it is final to obtain molecular engram paper chip；
(8) sample drop is placed 5~10 minutes in paper chip, adopts and be washed with distilled water 3 times, is detected；
Semiconductor-quantum-point is CdTe quantum, CdSe quantum dot or CdS quantum dot, and function monomer is Methacrylamide, third
Acrylamide, acrylic acid, methacrylic acid, crosslinking agent are ethylene glycol dimethacrylate, and initiator is azodiisobutyronitrile, mistake
Potassium sulfate, for pore-foaming agent using acetonitrile, methanol, isopropanol, organic solvent is dichloromethane or carbon tetrachloride；
The template molecule of synthesis molecular imprinting of organophosphorus pesticide residue polymer film, function monomer, crosslinking agent, pore-foaming agent, initiation
The amount ratio of the substance of agent and organic solvent is 0.1~0.5: 5: 0.5~5: 20~55: 0.1~0.5: 1.5~30, incorporation 2mg half
Conductor quantum dot.
2. the preparation method of molecular engram paper chip sensor according to claim 1, which is characterized in that paper is Chinese Shanghai
The Whatman chromatographic papers or ordinary filter paper of GE Healthcare Worldwide companies of Pudong, wax spray printer are applied for Fuji
Happy wax spray printer, a concentration of 10mmol/L of phosphate buffer solution contain 1.2mmol/L gold chlorides, 2.0mmol/L hexadecanes
Base trimethyl ammonium chloride and 7.2mmol/L hydrogen peroxide.
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Families Citing this family (8)
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| CN105675597B (en) * | 2016-01-19 | 2018-06-19 | 济南大学 | The preparation of a kind of three-dimensional colorimetric and optical electro-chemistry paper substrate equipment and its application in hydrogen peroxide detection |
| CN105924478B (en) * | 2016-05-24 | 2018-05-29 | 济南大学 | A kind of preparation method of three-dimensional paper substrate metal organic frame |
| CN106324065B (en) * | 2016-08-18 | 2018-11-20 | 济南大学 | A kind of preparation and organophosphorus insecticide detection of the photic electrochemical sensor of chemiluminescence |
| US10768158B2 (en) * | 2016-11-30 | 2020-09-08 | City University Of Hong Kong | Electrochemical detector |
| CN107024523A (en) * | 2017-04-25 | 2017-08-08 | 济南大学 | A kind of preparation and application of paper substrate optical electro-chemistry molecular engram sensor |
| CN107754614B (en) * | 2017-11-23 | 2020-07-24 | 苏州大学 | Method for performing hydrophilic-hydrophobic conversion by applying thiol-alkyne click reaction based on propiolic methacrylate porous membrane |
| CN109142289B (en) * | 2018-07-16 | 2021-01-22 | 佛山科学技术学院 | CsPbBr-based3Detection method of phoxim of perovskite quantum dot-molecular imprinting fluorescence sensor |
| CN113533475B (en) * | 2021-07-12 | 2023-11-14 | 武汉海关技术中心 | Multi-component sulfonamide antibiotic paper-based microfluidic analysis device and analysis method |
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